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EP0343444A2 - Cosmetic composition containing retinyl palmitate - Google Patents

Cosmetic composition containing retinyl palmitate Download PDF

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Publication number
EP0343444A2
EP0343444A2 EP89108536A EP89108536A EP0343444A2 EP 0343444 A2 EP0343444 A2 EP 0343444A2 EP 89108536 A EP89108536 A EP 89108536A EP 89108536 A EP89108536 A EP 89108536A EP 0343444 A2 EP0343444 A2 EP 0343444A2
Authority
EP
European Patent Office
Prior art keywords
cosmetic preparation
retinol palmitate
tetramethyl
cosmetic
palmitate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP89108536A
Other languages
German (de)
French (fr)
Other versions
EP0343444A3 (en
EP0343444B1 (en
Inventor
Elisabeth Dr. Siemer
Eckart Dr. Voss
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sara Lee DE NV
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Priority to AT89108536T priority Critical patent/ATE71286T1/en
Publication of EP0343444A2 publication Critical patent/EP0343444A2/en
Publication of EP0343444A3 publication Critical patent/EP0343444A3/en
Application granted granted Critical
Publication of EP0343444B1 publication Critical patent/EP0343444B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • Vitamin A retinol
  • Vitamin A has therefore long been recommended in cosmetic products for care for dry, flaky aging skin (see, for example, Reiss, F. and M. Campbell, Dermatologica 108 , 121 (1961)).
  • retinol has a direct pharmacological effect on the basal cells of the skin.
  • Scientific studies have shown that the topical use of retinol acetate increased the mitotic activity of the skin by 30%. A significant thickening of the epidermis was also demonstrated. Since the enzyme activity is also increased, the use of Retinol is particularly indicated in skin care products for aging skin, since numerous skin problems are caused by the too thin epidermis.
  • esters are mostly used in cosmetic preparations, preferably retinol acetate and retinol palmitate. Retinol acetate penetrates the skin more easily than palmitate, but is less stable in emulsions (Erlemann, GA, maschiner Journal, 7 (5), 28-38 (1985)).
  • the invention thus relates to a cosmetic preparation in liquid, semi-solid or solid form, preferably consisting of an oil-in-water or water-in-oil emulsion or an aqueous or oily solution or a gel or a stick or an aerosol as a basis , Retinol palmitate in an amount of 1,000 to 15,000 IU / g and 0.01-1% by weight of 3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane.
  • the preparation according to the invention preferably contains the retinol palmitate in a concentration of 2,000 to 7,000 IU / g, and 0.05 to 0.5% by weight of 3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane.
  • the cosmetic composition according to the invention contains carriers and auxiliaries typically used in cosmetic compositions, in particular antioxidants such as alpha-tocopherol, butylated hydroxyanisole, butylated hydroxytoluene and others
  • the carriers and auxiliaries also include solvents such as water, monoalcohols, low polyalcohols with 1-6 carbon atoms or mixtures thereof, furthermore fatty substances such as mineral, animal or vegetable oils or waxes, fatty acids, fatty alcohols, fatty acid esters, fatty alcohol ethers, oxyethylated fatty alcohols, Lanolin and derivatives, silicone oils.
  • solvents such as water, monoalcohols, low polyalcohols with 1-6 carbon atoms or mixtures thereof, furthermore fatty substances such as mineral, animal or vegetable oils or waxes, fatty acids, fatty alcohols, fatty acid esters, fatty alcohol ethers, oxyethylated fatty alcohols, Lanolin and derivatives, silicone oils.
  • the cosmetic agent according to the invention can also contain emulsifiers, which are nonionic, anionic, cationic or amphoteric compounds, e.g. Sterols, polyol fatty acid esters and fatty alcohol ethers, alkali or triethanolamine salts of fatty acids, sodium cetylstearyl sulfate, tetraacylammonium halides, phospholipids.
  • emulsifiers which are nonionic, anionic, cationic or amphoteric compounds, e.g. Sterols, polyol fatty acid esters and fatty alcohol ethers, alkali or triethanolamine salts of fatty acids, sodium cetylstearyl sulfate, tetraacylammonium halides, phospholipids.
  • thickeners can be used in the agent according to the invention. These include polyacrylic acid derivatives, cellulose derivatives, bentonites, xanthan derivatives, alginates, guar flour and locust bean flour.
  • the preparation according to the invention can contain further substances customary in cosmetic products. These include humectants, UV filters, dyes, buffer substances, preservatives and perfume oils.
  • Low polyalcohols such as glycerol, propylene glycol, butylene glycol, sorbitol, furthermore the 2-pyrrolidone-5-carboxylic acid and its sodium salt, lactic acid and its salts, urea, proteins and protein derivatives such as collagen, furthermore hyaluronic acid and others
  • Possible UV filters are preferably: benzylidene camphor compounds, p-aminobenzoic acid and their derivatives, anthranilates, cinnamates, salicylates, benzoxazole derivatives; Benzophenone derivatives, dibenzoylmethane derivatives, benzotriazole derivatives.
  • UV filters 2-ethoxyhexyl p- (dimethylamino) benzoate; 2-ethylhexyl p-methoxycinnamate; 3-benzylidene-d, 1-camphor; 3- (4'-methylbenzylidene) -d, 1-camphor; Amyl 4- (dimethylamino) benzoate; Homomenthyl salicylate; 2-hydroxy-4-methoxybenzophenone; N- (2-ethylhexyl) -4- (3'-methylidene camphor) benzenesulfonamide; N- (2-ethylhexyl) -3-benzylidene-10-kampfersulfonamid, optionally together with one of the following compounds: 4-tert-butyl-4'-methoxydibenzoylmethane; 5-isopropyldibenzoylmethane; ⁇ - (2-oxo-3-bornyliden
  • dyes to be added to the cosmetic preparations according to the invention are:
  • Possible preservatives are preferably: 2,4-hexadienoic acid (sorbic acid and its salts) 4-hydroxybenzoic acid, its salts and esters, 3-acetyl-6-methyl-2,4 (3H) pyranedione (dehydroacetic acid) and its salts 1,1-methylene-bis- (3- (1-hydroxy-methyl-2,4-dioximidazolidin-5-yl) urea) Imidazolidinyl urea 2-phenoxyethanol Benzyl alcohol.
  • the cosmetic agent according to the invention can be present as an emulsion (cream or milk), as an aqueous or oily solution, as an aqueous or oily gel, as a stick or as an aerosol. It can also be in any form that is suitable or customary for cosmetic skin care products.
  • the presentation is generally by mixing and stirring the components, optionally with subsequent homogenization.
  • Mixture I is melted at 75 ° C. and solution IV, which has been heated to the same temperature, is added with stirring. With further stirring and homogenization, the mixture is allowed to cool to 35 ° C., then mixture II and the perfume oil (III) are added, water is added to 100 g and the mixture is left to cool to room temperature with further stirring.
  • O / W emulsion (body milk) (In g)
  • the components of I are mixed with stirring.
  • the acrylamide / Na-acrylate copolymer II is then suspended uniformly in the mixture I with the Ultra-Turrax.
  • Solution III is emulsified in with rapid stirring, then the emulsion is homogenized.
  • Mixture I is melted at 75 ° C. and solution IV, which has been heated to the same temperature, is added with stirring. With further stirring and homogenization, the mixture is allowed to cool to 35 ° C., then the Mix II and the perfume oil (III) added, made up to 100 g with water and allowed to cool to room temperature with further stirring. The entire production takes place in an evacuated apparatus to avoid the incorporation of air.
  • the W / O emulsion (skin care product) is prepared in analogy to the information in Example 1.
  • the average uterine circumference (U) and, on the other hand, the average epidermis thickness are used to evaluate the results.
  • Test series 3 hexyl laurate as placebo
  • Test series 4 without treatment (O control).
  • Epidermis thickness (nm) Factor of increase in epidermal thickness Test series 1 78 36 64 67 4.5 Test series 2 120 55 45 49 3.3 Test series 3 216 99 1 37 2.5 control 218 100 0 15 1.0
  • the formulation according to the invention thus reduces the uterine diameter by an average of 64% and increases the epidermal thickness to 4.5 times the initial value, while the same amount of active substance on a neutral basis (test series 2) has much less improvements and the placebo series 3 has only very slight effects.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A cosmetic composition for local use based on retinyl palmitate (= vitamin A palmitate) is provided. The composition is characterised in that, besides customary vehicles and/or auxiliaries, it contains retinyl palmitate in an amount of 1,000 to 15,000 I.U./g and 0.01 to 1% by weight of 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane.

Description

Die Erfindung betrifft ein kosmetisches Präparat zur lo­kalen Anwendung auf Basis von Retinolpalmitat ( = Vita­min A-Palmitat).The invention relates to a cosmetic preparation for local use based on retinol palmitate (= vitamin A palmitate).

Ein Mangel an Vitamin A äußert sich in trockener, rau­her, verhornter Haut und Atrophie der Schweißdrüsen. Vitamin A (Retinol) wird deshalb seit langem in kos­metischen Mitteln zur Pflege bei trockener, schuppiger Altershaut empfohlen (siehe z.B. Reiss, F. und M. Camp­bell, Dermatologica 108, 121 (1961)).A lack of vitamin A manifests itself in dry, rough, calloused skin and atrophy of the sweat glands. Vitamin A (retinol) has therefore long been recommended in cosmetic products for care for dry, flaky aging skin (see, for example, Reiss, F. and M. Campbell, Dermatologica 108 , 121 (1961)).

Retinol übt neben seiner physiologischen Wirkung einen direkten pharmakologischen Effekt auf die Basalzellen der Haut aus. So wurde aufgrund wissenschaftlicher Un­tersuchungen nachgewiesen, daß bei topischer Anwendung von Retinolacetat die Mitoseaktivität der Haut um 30% gesteigert wurde. Ebenso konnte eine signifikante Ver­dickung der Epidermis nachgewiesen werden. Da auch die Enzymaktivität gesteigert wird, ist die Verwendung von Retinol besonders in Pflegepräparaten für die alternde Haut indiziert, da gerade zahlreiche Probleme der Al­tershaut durch die zu dünne Epidermis hervorgerufen werden.In addition to its physiological effect, retinol has a direct pharmacological effect on the basal cells of the skin. Scientific studies have shown that the topical use of retinol acetate increased the mitotic activity of the skin by 30%. A significant thickening of the epidermis was also demonstrated. Since the enzyme activity is also increased, the use of Retinol is particularly indicated in skin care products for aging skin, since numerous skin problems are caused by the too thin epidermis.

Wegen der geringen Stabilität von Retinol werden in kos­metischen Präparaten meist Ester eingesetzt, vorzugs­weise Retinolacetat und Retinolpalmitat. Retinolacetat penetriert leichter in die Haut als das Palmitat, ist allerdings in Emulsionen weniger stabil (Erlemann, G.A., Apotheker Journal, 7(5), 28-38 (1985)).Because of the low stability of retinol, esters are mostly used in cosmetic preparations, preferably retinol acetate and retinol palmitate. Retinol acetate penetrates the skin more easily than palmitate, but is less stable in emulsions (Erlemann, GA, Apotheker Journal, 7 (5), 28-38 (1985)).

Nach JANISTYN sind die in der Fachliteratur angegebenen unterschiedlichen Ergebnisse der Wirkung von Vitaminen nach deren topischer Applikation dadurch zu erklären, daß die Aufnahme der Vitamine durch die Haut trägerab­hängig ist (Janistyn, H., Handbuch der Kosmetika und Riechstoffe, III. Band: Die Körperpflegemittel, S. 614, Heidelberg 1973). Dies wird durch die Aussagen der Deut­schen Patentschrift DE 2609 575 C2 bestätigt, wonach die Mitosestimulierung der Haut durch Retinolacetat mittels Applikation in einer geeigneten Grundlage mit sehr viel niedrigeren Dosierungen erzielt werden kann als bei An­wendung des reinen Esters d.h. in Abwesenheit spezieller Zusatzstoffe.According to JANISTYN, the different results of the effects of vitamins after their topical application given in the specialist literature can be explained by the fact that the absorption of the vitamins through the skin is dependent on the wearer (Janistyn, H., Handbook of Cosmetics and Fragrances, Volume III: Personal Care Products , P. 614, Heidelberg 1973). This is confirmed by the statements of the German patent DE 2609 575 C2, according to which the mitosis stimulation of the skin by retinol acetate can be achieved by application in a suitable basis with much lower doses than when using the pure ester i.e. in the absence of special additives.

Im Gegensatz zum Retinolacetat konnte in derselben Ar­beit für Retinolpalmitat keine Wirkungssteigerung nach­gewiesen werden. Eine Erhöhung der Epidermisverdickung war nach dieser Arbeit auch durch Steigerung der Reti­nolpalmitatkonzentration nicht möglich.In contrast to retinol acetate, no increase in activity could be demonstrated in the same work for retinol palmitate. According to this work, an increase in epidermal thickening was not possible even by increasing the retinol palmitate concentration.

Dies bestätigt auch FLESCH, nach dem die zur Erhöhung der Epidermisdicke erforderlichen Retinolpalmitatdosen bei extrem hohen Werten von 50.000 bis 100.000 I.E./g liegen (FLESCH, P., J. Invest Dermatol. 19, 253 (1952)). Definition von I.E. (Internationale Einheit): 1 I.E. = 0,3µg Retinol (Vitamin A).This is also confirmed by FLESCH, according to which the doses of retinol palmitate required to increase the epidermis thickness are extremely high, from 50,000 to 100,000 IU / g (FLESCH, P., J. Invest Dermatol. 19, 253 (1952)). Definition of I.E. (International unit): 1 I.E. = 0.3µg retinol (vitamin A).

Überraschenderweise wurde jetzt gefunden, daß in einer die Verbindung 3,7,11,15-Tetramethyl-1,2,3-trihydroxy­hexadecan enthaltenden Grundlage eine epidermale Mitose­stimulierung und Epidermisverdickung schon mit sehr viel niedrigeren Retinolpalmitatdosen erzielt werden kann.Surprisingly, it has now been found that epidermal mitosis stimulation and epidermal thickening can be achieved with a much lower dose of retinol palmitate in a base containing the compound 3,7,11,15-tetramethyl-1,2,3-trihydroxyhexadecane.

Die Erfindung betrifft somit ein kosmetisches Präparat in flüssiger, halbfester oder fester Form, vorzugsweise bestehend aus einer Öl-in-Wasser- oder Wasser-in-Öl-­Emulsion oder einer wäßrigen oder öligen Lösung oder einem Gel oder einem Stift oder einem Aerosol als Grund­lage, Retinolpalmitat in einer Menge von 1.000 bis 15.000 I.E./g und 0,01 - 1 Gew.-% 3,7,11,15-Tetramethyl-­1,2,3-trihydroxy-hexadecan.The invention thus relates to a cosmetic preparation in liquid, semi-solid or solid form, preferably consisting of an oil-in-water or water-in-oil emulsion or an aqueous or oily solution or a gel or a stick or an aerosol as a basis , Retinol palmitate in an amount of 1,000 to 15,000 IU / g and 0.01-1% by weight of 3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane.

Das erfindungsgemäße Präparat enthält das Retinolpal­mitat vorzugsweise in einer Konzentration von 2.000 bis 7.000 I.E./g, und 0,05 bis 0,5 Gew.-% 3,7,11,15-Tetra­methyl-1,2,3-trihydroxy-hexadecan.The preparation according to the invention preferably contains the retinol palmitate in a concentration of 2,000 to 7,000 IU / g, and 0.05 to 0.5% by weight of 3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane.

Das erfindungsgemäße kosmetische Mittel enthält neben der o.a. Wirkstoffkombination üblicherweise in kos­metischen Mitteln eingesetzte Träger- und Hilfsstoffe, insbesondere Antioxidantien wie alpha-Tocopherol, Butyl­hydroxyanisol, Butylhydroxytoluol u.a.In addition to the combination of active ingredients mentioned above, the cosmetic composition according to the invention contains carriers and auxiliaries typically used in cosmetic compositions, in particular antioxidants such as alpha-tocopherol, butylated hydroxyanisole, butylated hydroxytoluene and others

Zu den Träger- und Hilfsstoffen zählen desweiteren Lö­sungsmittel wie Wasser, Monoalkohole, niedrige Polyalko­hole mit 1-6 Kohlenstoffatomen oder Mischungen davon, weiterhin Fettkörper, wie mineralische, tierische, oder pflanzliche Öle oder Wachse, Fettsäuren, Fettalkohole, Fettsäureester, Fettalkoholether, oxyethylierte Fettal­kohole, Lanolin und - Derivate, Silikonöle.The carriers and auxiliaries also include solvents such as water, monoalcohols, low polyalcohols with 1-6 carbon atoms or mixtures thereof, furthermore fatty substances such as mineral, animal or vegetable oils or waxes, fatty acids, fatty alcohols, fatty acid esters, fatty alcohol ethers, oxyethylated fatty alcohols, Lanolin and derivatives, silicone oils.

Das erfindungsgemäße kosmetische Mittel kann auch Emul­gatoren enthalten, wobei es sich um nichtionische, anio­nische, kationische oder amphotere Verbindungen handelt, z.B. Sterole, Polyol-Fettsäureester und -Fettalkohol­ether, Alkali- oder Triethanolaminsalze von Fettsäuren, Natriumcetylstearylsulfat, Tetraacylammoniumhalogenide, Phospholipide.The cosmetic agent according to the invention can also contain emulsifiers, which are nonionic, anionic, cationic or amphoteric compounds, e.g. Sterols, polyol fatty acid esters and fatty alcohol ethers, alkali or triethanolamine salts of fatty acids, sodium cetylstearyl sulfate, tetraacylammonium halides, phospholipids.

Ferner können Verdickungsmittel im erfindungsgemäßen Mittel eingesetzt sein. Dazu zählen Polyacrylsäurederi­vate, Cellulosederivate, Bentonite, Xanthanderivate, Alginate, Guarmehl und Johannisbrotmehl.Furthermore, thickeners can be used in the agent according to the invention. These include polyacrylic acid derivatives, cellulose derivatives, bentonites, xanthan derivatives, alginates, guar flour and locust bean flour.

Das erfindungsgemäße Präparat kann weitere in kosmeti­schen Mitteln übliche Stoffe enthalten. Dazu zählen Feuchthaltemittel, UV-Filter, Farbstoffe, Puffersub­stanzen, Konservierungsmittel und Parfümöle.The preparation according to the invention can contain further substances customary in cosmetic products. These include humectants, UV filters, dyes, buffer substances, preservatives and perfume oils.

Als Feuchthaltemittel seien beispielhaft aufgeführt:The following are examples of humectants:

Niedrige Polyalkohole wie Glycerin, Propylenglykol, Bu­tylenglykol, Sorbitol, des weiteren die 2-Pyrrolidon-5-­Carbonsäure und ihr Natriumsalz, Milchsäure und ihre Salze, Harnstoff, Proteine und Proteinderivate wie Col­lagen, des weiteren Hyaluronsäure u.a.Low polyalcohols such as glycerol, propylene glycol, butylene glycol, sorbitol, furthermore the 2-pyrrolidone-5-carboxylic acid and its sodium salt, lactic acid and its salts, urea, proteins and protein derivatives such as collagen, furthermore hyaluronic acid and others

Als UV-Filter kommen vorzugsweise in Frage: Benzyliden­kampferverbindungen, p-Aminobenzoesäure sowie ihre Deri­vate, Anthranilate, Cinnamate, Salicylate, Benzoxazol-­Derivate; Benzophenonderivate, Dibenzoylmethanderivate, Benzotriazol-Derivate.Possible UV filters are preferably: benzylidene camphor compounds, p-aminobenzoic acid and their derivatives, anthranilates, cinnamates, salicylates, benzoxazole derivatives; Benzophenone derivatives, dibenzoylmethane derivatives, benzotriazole derivatives.

Insbesondere setzt man die folgenden Verbindungen als UV-Filter ein:
2-Ethoxyhexyl-p-(dimethylamino)-benzoat;
2-Ethylhexyl-p-methoxycinnamat;
3-Benzyliden-d,1-kampfer;
3-(4′-Methylbenzyliden)-d,1-kampfer;
Amyl-4-(dimethylamino)-benzoat;
Homomenthylsalicylat;
2-Hydroxy-4-methoxybenzophenon;
N-(2-Ethylhexyl)-4-(3′-methylidenkampfer)-benzol­sulfonamid;
N-(2-Ethylhexyl)-3-benzyliden-10-kampfersulfonamid, ge­gebenenfalls zusammen mit einer der folgenden Verbindun­gen:
4-tert.-Butyl-4′methoxydibenzoylmethan;
5-Isopropyldibenzoylmethan;
α-(2-Oxo-3-bornyliden)-toluol-4-sulfonsäure und die Salze davon;
α-(2-Oxo-3-bornyliden)-p-xylol-2-sulfonsäure;
2-Hydroxy-4-methoxybenzophenon-5-sulfonsäure;
4-[(2-Oxo-3-bornyliden)-methyl)-phenyltrimethyl­ammoniummethylsulfat;
1,4-Di-[sulfocamphorylmethyliden]-benzolsäure;
2-Phenylbenzimidazol-5-sulfonsäure.In particular, the following compounds are used as UV filters:
2-ethoxyhexyl p- (dimethylamino) benzoate;
2-ethylhexyl p-methoxycinnamate;
3-benzylidene-d, 1-camphor;
3- (4'-methylbenzylidene) -d, 1-camphor;
Amyl 4- (dimethylamino) benzoate;
Homomenthyl salicylate;
2-hydroxy-4-methoxybenzophenone;
N- (2-ethylhexyl) -4- (3'-methylidene camphor) benzenesulfonamide;
N- (2-ethylhexyl) -3-benzylidene-10-kampfersulfonamid, optionally together with one of the following compounds:
4-tert-butyl-4'-methoxydibenzoylmethane;
5-isopropyldibenzoylmethane;
α- (2-oxo-3-bornylidene) toluene-4-sulfonic acid and the salts thereof;
α- (2-oxo-3-bornylidene) -p-xylene-2-sulfonic acid;
2-hydroxy-4-methoxybenzophenone-5-sulfonic acid;
4 - [(2-oxo-3-bornylidene) methyl) phenyltrimethylammonium methyl sulfate;
1,4-di- [sulfocamphorylmethylidene] benzene acid;
2-phenylbenzimidazole-5-sulfonic acid.

Als den erfindungsgemäßen kosmetischen Präparaten zu­zusetzenden Farbstoffe seien beispielhaft aufgeführt:Examples of dyes to be added to the cosmetic preparations according to the invention are:

Farbe L Rot 4, Farbe C Grün 11, Farbe L Blau 3, Sicomet Gelborange 85, Sicomet Patentblau, Sicopharm Gelb 10.Color L Red 4, Color C Green 11, Color L Blue 3, Sicomet Yellow Orange 85, Sicomet Patent Blue, Sicopharm Yellow 10.

Als Konservierungsmittel kommen vorzugsweise in Frage:
2,4-Hexadiensäure (Sorbinsäure und ihre Salze)
4-Hydroxybenzoesäure, ihre Salze und Ester,
3-Acetyl-6-methyl-2,4(3H)-pyrandion (Dehydracetsäure) und seine Salze
1,1-Methylen-bis-(3-(1-hydroxy-methyl-2,4-­dioximidazolidin-5-yl)harnstoff)
Imidazolidinylharnstoff
2-Phenoxy-ethanol
Benzylalkohol.Possible preservatives are preferably:
2,4-hexadienoic acid (sorbic acid and its salts)
4-hydroxybenzoic acid, its salts and esters,
3-acetyl-6-methyl-2,4 (3H) pyranedione (dehydroacetic acid) and its salts
1,1-methylene-bis- (3- (1-hydroxy-methyl-2,4-dioximidazolidin-5-yl) urea)
Imidazolidinyl urea
2-phenoxyethanol
Benzyl alcohol.

Das erfindungsgemäße kosmetische Mittel kann als Emul­sion (Creme oder Milch), als wäßrige oder ölige Lösung, als wäßriges oder öliges Gel, als Stift oder auch als Aerosol vorliegen. Es kann zudem in jeder Form vorliegen, die für kosmetische Hautpflegemittel geeignet oder üblich ist. Die Darstellung erfolgt i.a. durch Mischen und Rühren der Komponenten, gegebenenfalls mit anschließendem Homogenisieren.The cosmetic agent according to the invention can be present as an emulsion (cream or milk), as an aqueous or oily solution, as an aqueous or oily gel, as a stick or as an aerosol. It can also be in any form that is suitable or customary for cosmetic skin care products. The presentation is generally by mixing and stirring the components, optionally with subsequent homogenization.

Die Erfindung wird im folgenden anhand der Beispiele näher erläutert, ohne daß dies einschränkenden Charakter haben soll.The invention is explained in more detail below with reference to examples, without this being intended to be restrictive.

Beispiel 1example 1

O/W-Emulsion (Feuchtigkeitscreme) O / W emulsion (moisturizer) (Angaben in g)(In g) I.I. Polyoxyethylen-12-CetylstearylalkoholPolyoxyethylene-12-cetylstearyl alcohol 3,03.0 Palmitin-/Stearinsäure-Mono/DiglyceridePalmitic / stearic acid mono / diglycerides 8,08.0 2-Octyldodecanol2-octyldodecanol 10,010.0 Capryl-/CaprinsäuretriglyceridCaprylic / capric acid triglyceride 5,05.0 Paraffinöl, dickflüssigParaffin oil, viscous 4,04.0 II.II. RetinalpalmitatRetinal palmitate 500.000 I.E.500,000 IU alpha-Tocopherol (Vitamin E)alpha-tocopherol (vitamin E) 0,10.1 3,7,11,15-Tetramethyl-1,2,3-trihydroxy-hexadecan3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane 0,10.1 III.III. ParfümölPerfume oil q.s.q.s. IV.IV. GlycerinGlycerin 7,07.0 KonservierungsmittelPreservative q.s.q.s. Wasserwater ad 100,00ad 100.00

Herstellung:Manufacturing:

Die Mischung I wird bei 75°C zum Schmelzen gebracht und die auf die gleiche Temperatur erwärmte Lösung IV unter Rühren zugegeben. Unter weiterem Rühren und Homogeni­sieren läßt man auf 35°C abkühlen, dann gibt man die Mischung II und das Parfümöl (III) hinzu, ergänzt mit Wasser auf 100 g und läßt unter weiterem Rühren auf Raumtemperatur abkühlen.Mixture I is melted at 75 ° C. and solution IV, which has been heated to the same temperature, is added with stirring. With further stirring and homogenization, the mixture is allowed to cool to 35 ° C., then mixture II and the perfume oil (III) are added, water is added to 100 g and the mixture is left to cool to room temperature with further stirring.

Die gesamte Herstellung erfolgt unter Vakuum-­Bedingungen, um das Einarbeiten von Luft zu vermeiden.The entire production takes place under vacuum conditions in order to avoid the incorporation of air.

Beispiel 2Example 2

O/W-Emulsion (Körpermilch) O / W emulsion (body milk) (Angaben in g)(In g) I.I. Mono-, Di- u. Tri(alkyltetraglykolether)-o-phosphorsäureesterMono-, Di- and. Tri (alkyl tetraglycol ether) o-phosphoric acid esters 3,03.0 Paraffinöl, dünnflüssigParaffin oil, thin 3,03.0 IsopropylpalmitatIsopropyl palmitate 3,03.0 JojobaölJojoba oil 5,05.0 RetinolpalmitatRetinol palmitate 500.000 I.E.500,000 IU ButylhydroxytoluolButylated hydroxytoluene 0,010.01 3,7,11,15-Tetramethyl-1,2,3-trihydroxy-hexadecan3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane 0,10.1 ParfümölPerfume oil q.s.q.s. II.II. Acrylamid/Na-acrylat-CopolymerAcrylamide / Na acrylate copolymer 0,60.6 III.III. GlycerinGlycerin 3,03.0 KonservierungsmittelPreservative q.s.q.s. Wasserwater ad 100,0ad 100.0

Herstellung:Manufacturing:

Die Bestandteile von I werden unter Rühren gemischt. An­schließend wird das Acrylamid/Na-acrylat-Copolymer II mit dem Ultra-Turrax gleichmäßig in der Mischung I sus­pendiert. Die Lösung III wird unter schnellem Rühren einemulgiert, dann wird die Emulsion homogenisiert.The components of I are mixed with stirring. The acrylamide / Na-acrylate copolymer II is then suspended uniformly in the mixture I with the Ultra-Turrax. Solution III is emulsified in with rapid stirring, then the emulsion is homogenized.

Beispiel 3Example 3

W/O-Emulsion (Nachtcreme) W / O emulsion (night cream) (Angabe in g)(In g) I.I. Polyethylenglycol-1-Glycerol-Sorbitan-IsostearatPolyethylene glycol 1 glycerol sorbitan isostearate 10,010.0 BienenwachsBeeswax 3,03.0 Lanolinlanolin 3,03.0 Capryl-/CaprinsäuretriglyceridCaprylic / capric acid triglyceride 11,011.0 PerhydrosqualenPerhydroscalene 11,011.0 WeizenkeimölWheat germ oil 3,03.0 II.II. RetinolpalmitatRetinol palmitate 500.000 I.E.500,000 IU ButylhydroxyanisolButylated hydroxyanisole 0,010.01 3,7,11,15-Tetramethyl-1,2,3-trihydroxy-hexadecan3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane 0,10.1 III.III. ParfümölPerfume oil q.s.q.s. IV.IV. GlycerinGlycerin 2,02.0 KonservierungsmittelPreservative q.s.q.s. MagnesiumsulfatMagnesium sulfate 0,70.7 Wasserwater ad 100,0ad 100.0

Herstellung:Manufacturing:

Die Mischung I wird bei 75°C zum Schmelzen gebracht und die auf die gleiche Temperatur erwärmte Lösung IV unter Rühren zugegeben. Unter weiterem Rühren und Homogeni­sieren läßt man auf 35°C abkühlen, dann gibt man die Mischung II und das Parfümöl (III) hinzu, ergänzt mit Wasser auf 100 g und läßt unter weiterem Rühren auf Raumtemperatur abkühlen. Die gesamte Herstellung erfolgt in einer evakuierten Apparatur, um das Einarbeiten von Luft zu vermeiden.Mixture I is melted at 75 ° C. and solution IV, which has been heated to the same temperature, is added with stirring. With further stirring and homogenization, the mixture is allowed to cool to 35 ° C., then the Mix II and the perfume oil (III) added, made up to 100 g with water and allowed to cool to room temperature with further stirring. The entire production takes place in an evacuated apparatus to avoid the incorporation of air.

Beispiel 4Example 4

W/O-Emulsion (Hautpflegemilch) W / O emulsion (skin care milk) (Angaben in g)(In g) I.I. Polyoxypropylen-1,5-polyoxyethylen-2,5-glycerol-Sorbitan-HydroxystearatPolyoxypropylene-1,5-polyoxyethylene-2,5-glycerol sorbitan hydroxystearate 6,06.0 Polyoxypropylen(15)-stearylether/CyclomethiconePolyoxypropylene (15) stearyl ether / cyclomethicone 6,06.0 Paraffin, dünnflüssigParaffin, thin 12,012.0 II.II. RetinolpalmitatRetinol palmitate 500.000 I.E.500,000 IU alpha-Tocopherol (Vitamin E)alpha-tocopherol (vitamin E) 0,10.1 3,7,11,15-Tetramethyl-1,2,3-trihydroxy-hexadecan3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane 0,10.1 III.III. ParfümölPerfume oil q.s.q.s. IV.IV. Polyethylenglycol-SorbitolPolyethylene glycol sorbitol 4,04.0 MagnesiumsulfatMagnesium sulfate 0,70.7 KonservierungsmittelPreservative q.s.q.s. Wasserwater ad 100,0ad 100.0

Die Herstellung der W/O-Emulsion (Hautpflegemittel) erfolgt in Analogie zu den Angaben von Beispiel 1.The W / O emulsion (skin care product) is prepared in analogy to the information in Example 1.

WIRKSAMKEITSVERGLEICHEFFECTIVENESS COMPARISON 1. Meßverfahren1. Measuring method

Für jede Versuchsreihe werden 5 weiblichen Rhinomäusen (Alter 7-9 Wochen) täglich je 0.025 ml der Testlösung topisch appliziert. Die Versuchsdauer beträgt 9 Tage. Danach werden Zellschnitte von Biopsien der behandelten Haut optisch vermessen und ausgewertet.For each series of tests, 5 female rhinomice (ages 7-9 weeks) each topically applied 0.025 ml of the test solution. The duration of the experiment is 9 days. Then cell sections from biopsies of the treated skin are optically measured and evaluated.

Zur Ergebnisbewertung werden einerseits der durch­schnittliche Utriculumumfang (U), andererseits die durchschnittliche Epidermisdicke herangezogen.On the one hand, the average uterine circumference (U) and, on the other hand, the average epidermis thickness are used to evaluate the results.

Folgende Versuchsreihen soll die Wirkung der erfindungs­gemäßen Rezepturen verdeutlichen:The following test series are intended to illustrate the effect of the formulations according to the invention:

Versuchsreihe 1:Test series 1:

Gemisch ausMixture of 5000 I.E./g5000 IU / g RetinolpalmitatRetinol palmitate 0,1 Gew.-%0.1% by weight 3,7,11,15-Tetramethyl-1,2,3-trihydroxy-hexadecan (= Phytantriol)3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane (= phytantriol) 0,1 Gew.-%0.1% by weight alpha-Tocopherol ( = Vitamin E) in Laurinsäurehexylesteralpha-tocopherol (= vitamin E) in hexyl laurate

Versuchsbeispiel 2.Experimental example 2.

Gemisch ausMixture of 5000 I.E./g5000 IU / g Vitamin-A-Palmitat in LaurinsäurehexylesterVitamin A palmitate in hexyl laurate

Versuchsreihe 3: Laurinsäurehexylester als Placebo Test series 3: hexyl laurate as placebo Versuchsreihe 4: ohne Behandlung (O-Kontrolle). Test series 4: without treatment (O control). 2. Ergebnisse:2 results:

Durchmesser U (nm)Diameter U (nm) %-Durchmesser U der Kontrolle% Diameter U of the control Wirksamkeit (in %)Effectiveness (in%) Epidermis Dicke (nm)Epidermis thickness (nm) Faktor der Zunahme der EpidermisdickeFactor of increase in epidermal thickness Versuchsreihe 1Test series 1 7878 3636 6464 6767 4,54.5 Versuchsreihe 2Test series 2 120120 5555 4545 4949 3,33.3 Versuchsreihe 3Test series 3 216216 9999 11 3737 2,52.5 Kontrollecontrol 218218 100100 00 1515 1,01.0

Die erfindungsgemäße Rezeptur verringert somit die Utrikulumdurchmesser im Durchschnitt um 64% und erhöht die Epidermisdicke auf das 4,5 fache des Ausgangswertes, während die gleiche Wirkstoffmenge in neutraler Grund­lage (Versuchsreihe 2) wesentlich geringere Verbesserun­gen und die Placeboreihe 3 nur sehr geringe Effekte auf­weist.The formulation according to the invention thus reduces the uterine diameter by an average of 64% and increases the epidermal thickness to 4.5 times the initial value, while the same amount of active substance on a neutral basis (test series 2) has much less improvements and the placebo series 3 has only very slight effects.

Claims (5)

1. Kosmetisches Präparat auf Basis von Retinolpalmi­tat in flüssiger, halbfester oder fester Form, da­durch gekennzeichnet, daß es neben üblichen Trägern und/oder Hilfsstoffen Retinolpalmitat in einer Men­ge von 1000 bis 15000 I.E./g und 0,01 bis 1 Ge­wichtsprozent 3,7,11,15-Tetramethyl-1,2,3-trihydro­xyhexadecan enthält.1. Cosmetic preparation based on retinol palmitate in liquid, semi-solid or solid form, characterized in that it contains retinol palmitate in an amount of 1000 to 15000 IU / g and 0.01 to 1 percent by weight 3.7 in addition to conventional carriers and / or auxiliaries. Contains 11,15-tetramethyl-1,2,3-trihydroxyhexadecane. 2. Kosmetisches Präparat gemäß Anspruch 1, dadurch ge­kennzeichnet, daß es sich um eine Öl-in-Wasser-­Emulsion, Wasser-in-Öl-Emulsion, eine wäßrige oder ölige Lösung, ein Gel, einen Stift oder ein Aerosol handelt.2. Cosmetic preparation according to claim 1, characterized in that it is an oil-in-water emulsion, water-in-oil emulsion, an aqueous or oily solution, a gel, a stick or an aerosol. 3. Kosmetisches Präparat gemäß Anspruch 1, dadurch ge­kennzeichnet, daß es 2000 bis 5000 I.E./g Retinol­palmitat und 0,05 bis 0,5 Gew.-% 3,7,11,15-Tetra­methyl-1,2,3-trihydroxy-hexadecan enthält.3. Cosmetic preparation according to claim 1, characterized in that it is 2000 to 5000 IU / g retinol palmitate and 0.05 to 0.5 wt .-% 3,7,11,15-tetramethyl-1,2,3-trihydroxy- contains hexadecane. 4. Kosmetisches Präparat gemäß Anspruch 1 bis 3, da­durch gekennzeichnet, daß es als Träger- und/oder Hilfsstoffe einen oder mehreren der folgenden Stof­fe enthält: Antioxidantien, Lösungsmittel, minera­lische, tierische oder pflanzliche Öle oder Wachse, Fettsäuren, Fettalkohole, Fettsäureester, Fettalko­holether, oxyethylierte Fettalkohole, Lanolin oder Lanolinderivate, Siliconöle, Emulgatoren, Verdik­kungsmittel, Feuchthaltemittel, UV-Filter, Farb­stoffe, Puffersubstanzen, Konservierungsmittel und Parfümöle.4. Cosmetic preparation according to claim 1 to 3, characterized in that it contains as carrier and / or auxiliary substances one or more of the following substances: antioxidants, solvents, mineral, animal or vegetable oils or waxes, fatty acids, fatty alcohols, fatty acid esters, fatty alcohol ethers , oxyethylated fatty alcohols, lanolin or lanolin derivatives, silicone oils, emulsifiers, thickeners, humectants, UV filters, dyes, buffer substances, preservatives and perfume oils. 5. Verfahren zur Herstellung von kosmetischen Präpa­raten auf Basis von Retinolpalmitat, dadurch ge­kennzeichnet, daß man pro g des kosmetischen Prä­parates 1000 bis 15000 I.E. Retinol-palmitat und bezogen auf das kosmetische Präparat 0,01 bis 1 Gew.-% 3,7,11,15-Tetramethyl-1,2,3-trihydroxy-hexa­decan mit üblichen Träger- und/oder Hilfsstoffen gegebenenfalls unter Rühren und/oder Homogenisieren vermischt.5. A process for the production of cosmetic preparations based on retinol palmitate, characterized in that 1000 to 15000 IU per g of the cosmetic preparation. Retinol palmitate and, based on the cosmetic preparation, 0.01 to 1% by weight of 3,7,11,15-tetramethyl-1,2,3-trihydroxy-hexadecane with conventional carriers and / or auxiliaries, if appropriate with stirring and / or homogenizing mixed.
EP89108536A 1988-05-25 1989-05-12 Cosmetic composition containing retinyl palmitate Expired - Lifetime EP0343444B1 (en)

Priority Applications (1)

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AT89108536T ATE71286T1 (en) 1988-05-25 1989-05-12 COSMETIC PREPARATION BASED ON RETINOL PALMITATE.

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DE3817623A DE3817623A1 (en) 1988-05-25 1988-05-25 COSMETIC PREPARATION BASED ON RETINOL PALMITATE

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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0440398A1 (en) * 1990-01-29 1991-08-07 JOHNSON & JOHNSON CONSUMER PRODUCTS, INC. Skin care compositions
WO1992001439A1 (en) * 1990-07-17 1992-02-06 Maja Zeidler A concentrate for skin lotions, creams, and similar skin preparations
FR2675045A1 (en) * 1991-04-10 1992-10-16 Carita Sa Cosmetic composition having an antidehydrating effect which is usable in lipsticks
WO1993015708A1 (en) * 1992-02-18 1993-08-19 L'oreal Cosmetic and/or pharmaceutical composition containing a dispersion of lipidic vesicles, process for the preparation of said dispersion, and lipidic vesicle dispersion
EP0579078A1 (en) * 1992-07-16 1994-01-19 Bayer Ag Cosmetic sunscreen
EP0579079A1 (en) * 1992-07-16 1994-01-19 Bayer Ag Cosmetic preparation for treating light-induced skin ageing
EP0666076A2 (en) * 1993-12-30 1995-08-09 L'oreal Water in oil emulsion containing retinol
WO1996007396A2 (en) * 1994-09-07 1996-03-14 Johnson & Johnson Consumer Products, Inc. Retinoid compositions
WO1997031620A2 (en) * 1996-03-01 1997-09-04 Johnson & Johnson Consumer Products, Inc. Topical compositions comprising an oil-in-water emulsion and a retinoid
US5976555A (en) * 1994-09-07 1999-11-02 Johnson & Johnson Consumer Products, Inc. Topical oil-in-water emulsions containing retinoids
US6193956B1 (en) 1995-09-06 2001-02-27 Johnson & Johnson Consumer Companies, Inc. Topical compositions
USH2043H1 (en) 1997-05-23 2002-08-06 The Procter & Gamble Company Skin care compositions
US6444647B1 (en) 1999-04-19 2002-09-03 The Procter & Gamble Company Skin care compositions containing combination of skin care actives
US6531141B1 (en) 2000-03-07 2003-03-11 Ortho-Mcneil Pharmaceutical, Inc. Oil-in-water emulsion containing tretinoin
US7459288B2 (en) 2002-11-11 2008-12-02 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method of producing retinyl esters
WO2018111952A1 (en) 2016-12-13 2018-06-21 The Procter & Gamble Company Stable personal care compositions containing a retinoid

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DE4417038A1 (en) * 1994-05-14 1995-11-16 Carl Heinrich Dr Weischer New retinyl lipoate esters

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Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0440398A1 (en) * 1990-01-29 1991-08-07 JOHNSON & JOHNSON CONSUMER PRODUCTS, INC. Skin care compositions
WO1992001439A1 (en) * 1990-07-17 1992-02-06 Maja Zeidler A concentrate for skin lotions, creams, and similar skin preparations
FR2675045A1 (en) * 1991-04-10 1992-10-16 Carita Sa Cosmetic composition having an antidehydrating effect which is usable in lipsticks
US5626868A (en) * 1992-02-18 1997-05-06 L'oreal Cosmetic and/or pharmaceutical composition containing a dispersion of lipid vesicles, process for the preparation of the said dispersion and dispersion of lipid vesicles
WO1993015708A1 (en) * 1992-02-18 1993-08-19 L'oreal Cosmetic and/or pharmaceutical composition containing a dispersion of lipidic vesicles, process for the preparation of said dispersion, and lipidic vesicle dispersion
FR2687314A1 (en) * 1992-02-18 1993-08-20 Oreal LIPID VESICLE DISPERSION, COSMETIC AND / OR PHARMACEUTICAL COMPOSITION CONTAINING THE SAME, AND PROCESS FOR THE PREPARATION OF SAID DISPERSION.
US5443840A (en) * 1992-02-18 1995-08-22 L'oreal Cosmetic and/or pharmaceutical composition containing a dispersion of lipid vesicles, process for the preparation of the said dispersion and dispersion of lipid vesicles
EP0579078A1 (en) * 1992-07-16 1994-01-19 Bayer Ag Cosmetic sunscreen
EP0579079A1 (en) * 1992-07-16 1994-01-19 Bayer Ag Cosmetic preparation for treating light-induced skin ageing
US5372805A (en) * 1992-07-16 1994-12-13 Bayer Aktiengesellschaft Cosmetic sunscreen
AU663787B2 (en) * 1992-07-16 1995-10-19 Sara Lee/De N.V. Cosmetic sunscreen
EP0953338A1 (en) * 1993-12-30 1999-11-03 L'oreal Packaging device for a product
EP0666076A3 (en) * 1993-12-30 1997-01-02 Oreal Water in oil emulsion containing retinol.
EP0666076A2 (en) * 1993-12-30 1995-08-09 L'oreal Water in oil emulsion containing retinol
WO1996007396A2 (en) * 1994-09-07 1996-03-14 Johnson & Johnson Consumer Products, Inc. Retinoid compositions
WO1996007396A3 (en) * 1994-09-07 1996-07-18 Jonhson & Johnson Consumer Pro Retinoid compositions
US6461622B2 (en) 1994-09-07 2002-10-08 Johnson & Johnson Consumer Companies, Inc. Topical compositions
US5976555A (en) * 1994-09-07 1999-11-02 Johnson & Johnson Consumer Products, Inc. Topical oil-in-water emulsions containing retinoids
US6193956B1 (en) 1995-09-06 2001-02-27 Johnson & Johnson Consumer Companies, Inc. Topical compositions
WO1997031620A2 (en) * 1996-03-01 1997-09-04 Johnson & Johnson Consumer Products, Inc. Topical compositions comprising an oil-in-water emulsion and a retinoid
WO1997031620A3 (en) * 1996-03-01 1998-01-08 Johnson & Johnson Consumer Topical compositions comprising an oil-in-water emulsion and a retinoid
USH2043H1 (en) 1997-05-23 2002-08-06 The Procter & Gamble Company Skin care compositions
US6444647B1 (en) 1999-04-19 2002-09-03 The Procter & Gamble Company Skin care compositions containing combination of skin care actives
US6531141B1 (en) 2000-03-07 2003-03-11 Ortho-Mcneil Pharmaceutical, Inc. Oil-in-water emulsion containing tretinoin
US7459288B2 (en) 2002-11-11 2008-12-02 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method of producing retinyl esters
US8030352B2 (en) 2002-11-11 2011-10-04 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Method of producing retinyl esters
WO2018111952A1 (en) 2016-12-13 2018-06-21 The Procter & Gamble Company Stable personal care compositions containing a retinoid

Also Published As

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DE3817623A1 (en) 1989-11-30
DE58900685D1 (en) 1992-02-20
ES2029362T3 (en) 1992-08-01
ATE71286T1 (en) 1992-01-15
EP0343444A3 (en) 1990-01-31
EP0343444B1 (en) 1992-01-08

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